CZ293875B6 - Způsob přípravy alkylovaných kyanoderivátů v přítomnosti trialkylaminů nebo trialkylfosfinů - Google Patents

Způsob přípravy alkylovaných kyanoderivátů v přítomnosti trialkylaminů nebo trialkylfosfinů Download PDF

Info

Publication number: CZ293875B6
Authority: CZ; Czechia
Prior art keywords: carbon atoms; formula; alkyl; alkyl group; group containing
Prior art date: 1997-12-17

Application number

CZ19984148A

Other languages

Czech (cs)

English (en)

Other versions

CZ414898A3 (cs

Inventor

Korbágerhard

Flemmingáhans@Wolfram

Lehnertárudolf

Original Assignee

AventisÁPharmaÁDeutschlandÁGmbH

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1997-12-17

Filing date

1998-12-15

Publication date

2004-08-18

1997-12-17 Priority claimed from DE1997156091 external-priority patent/DE19756091A1/de

1998-01-29 Priority claimed from DE1998103408 external-priority patent/DE19803408A1/de

1998-12-15 Application filed by AventisÁPharmaÁDeutschlandÁGmbH filed Critical AventisÁPharmaÁDeutschlandÁGmbH

1999-07-14 Publication of CZ414898A3 publication Critical patent/CZ414898A3/cs

2004-08-18 Publication of CZ293875B6 publication Critical patent/CZ293875B6/cs

Links

125000004093 cyano group Chemical group *C#N 0.000 title claims abstract description 12
125000005270 trialkylamine group Chemical group 0.000 title abstract description 6
238000004519 manufacturing process Methods 0.000 title abstract 2
150000003003 phosphines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 37
239000002168 alkylating agent Substances 0.000 claims abstract description 13
229940100198 alkylating agent Drugs 0.000 claims abstract description 13
239000003795 chemical substances by application Substances 0.000 claims abstract description 8
125000004432 carbon atom Chemical group C* 0.000 claims description 89
125000000217 alkyl group Chemical group 0.000 claims description 62
238000000034 method Methods 0.000 claims description 25
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 14
-1 methylenedioxy Chemical group 0.000 claims description 13
238000002360 preparation method Methods 0.000 claims description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
229910052799 carbon Inorganic materials 0.000 claims description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
125000005843 halogen group Chemical group 0.000 claims description 8
238000005804 alkylation reaction Methods 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 7
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 6
GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 claims description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims description 6
239000002202 Polyethylene glycol Substances 0.000 claims description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 6
125000003545 alkoxy group Chemical group 0.000 claims description 6
230000029936 alkylation Effects 0.000 claims description 6
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 claims description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
229920001223 polyethylene glycol Polymers 0.000 claims description 6
229920001451 polypropylene glycol Polymers 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
PGQTYXFMSZUGOW-UHFFFAOYSA-N 2-methyl-2-phenylpropanenitrile Chemical compound N#CC(C)(C)C1=CC=CC=C1 PGQTYXFMSZUGOW-UHFFFAOYSA-N 0.000 claims description 5
XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
IGNTWNVBGLNYDV-UHFFFAOYSA-N triisopropylphosphine Chemical compound CC(C)P(C(C)C)C(C)C IGNTWNVBGLNYDV-UHFFFAOYSA-N 0.000 claims description 5
RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 claims description 5
KVZJLSYJROEPSQ-UHFFFAOYSA-N 1,2-dimethylcyclohexane Chemical compound CC1CCCCC1C KVZJLSYJROEPSQ-UHFFFAOYSA-N 0.000 claims description 4
SGVUHPSBDNVHKL-UHFFFAOYSA-N 1,3-dimethylcyclohexane Chemical compound CC1CCCC(C)C1 SGVUHPSBDNVHKL-UHFFFAOYSA-N 0.000 claims description 4
HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 claims description 4
AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 claims description 4
PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 claims description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 4
BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 claims description 4
UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 claims description 4
239000002904 solvent Substances 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 4
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
ZLFQTZYFXYOGLS-UHFFFAOYSA-N 1-methyl-4-phenylpiperidine-4-carbonitrile Chemical compound C1CN(C)CCC1(C#N)C1=CC=CC=C1 ZLFQTZYFXYOGLS-UHFFFAOYSA-N 0.000 claims description 3
150000008050 dialkyl sulfates Chemical class 0.000 claims description 3
IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims description 3
150000002430 hydrocarbons Chemical class 0.000 claims description 3
HAWPXGHAZFHHAD-UHFFFAOYSA-N mechlorethamine Chemical compound ClCCN(C)CCCl HAWPXGHAZFHHAD-UHFFFAOYSA-N 0.000 claims description 3
WYZDCUGWXKHESN-UHFFFAOYSA-N n-benzyl-n-methyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(C)CC1=CC=CC=C1 WYZDCUGWXKHESN-UHFFFAOYSA-N 0.000 claims description 3
239000003960 organic solvent Substances 0.000 claims description 3
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 claims description 3
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 claims description 2
KBNFGTQCYBBZJA-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]-2-methylpropane Chemical compound CCOCCOCCOC(C)(C)C KBNFGTQCYBBZJA-UHFFFAOYSA-N 0.000 claims description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
RJFAYQIBOAGBLC-BYPYZUCNSA-N Selenium-L-methionine Chemical compound C[Se]CC[C@H](N)C(O)=O RJFAYQIBOAGBLC-BYPYZUCNSA-N 0.000 claims description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
150000001347 alkyl bromides Chemical class 0.000 claims description 2
150000001348 alkyl chlorides Chemical class 0.000 claims description 2
150000001349 alkyl fluorides Chemical class 0.000 claims description 2
150000001350 alkyl halides Chemical class 0.000 claims description 2
150000001351 alkyl iodides Chemical class 0.000 claims description 2
150000001450 anions Chemical group 0.000 claims description 2
150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 claims description 2
LMEDOLJKVASKTP-UHFFFAOYSA-N dibutyl sulfate Chemical compound CCCCOS(=O)(=O)OCCCC LMEDOLJKVASKTP-UHFFFAOYSA-N 0.000 claims description 2
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 claims description 2
229940008406 diethyl sulfate Drugs 0.000 claims description 2
QUJIVWINNPEYAS-UHFFFAOYSA-N dihexyl sulfate Chemical compound CCCCCCOS(=O)(=O)OCCCCCC QUJIVWINNPEYAS-UHFFFAOYSA-N 0.000 claims description 2
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 claims description 2
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 claims description 2
GAFRWLVTHPVQGK-UHFFFAOYSA-N dipentyl sulfate Chemical compound CCCCCOS(=O)(=O)OCCCCC GAFRWLVTHPVQGK-UHFFFAOYSA-N 0.000 claims description 2
150000002170 ethers Chemical class 0.000 claims description 2
229960003750 ethyl chloride Drugs 0.000 claims description 2
MFKHKJMRWGOTHL-UHFFFAOYSA-M ethyl(trioctyl)azanium;chloride Chemical compound [Cl-].CCCCCCCC[N+](CC)(CCCCCCCC)CCCCCCCC MFKHKJMRWGOTHL-UHFFFAOYSA-M 0.000 claims description 2
PPMPHRIJIMNDPU-UHFFFAOYSA-M ethyl(trioctyl)phosphanium;chloride Chemical compound [Cl-].CCCCCCCC[P+](CC)(CCCCCCCC)CCCCCCCC PPMPHRIJIMNDPU-UHFFFAOYSA-M 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
ZFIUCZXOGNIMCP-UHFFFAOYSA-M methyl(trioctyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZFIUCZXOGNIMCP-UHFFFAOYSA-M 0.000 claims description 2
GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 claims description 2
FRQONEWDWWHIPM-UHFFFAOYSA-N n,n-dicyclohexylcyclohexanamine Chemical compound C1CCCCC1N(C1CCCCC1)C1CCCCC1 FRQONEWDWWHIPM-UHFFFAOYSA-N 0.000 claims description 2
LYYLWJOKAQADDU-UHFFFAOYSA-N n,n-dihexadecylhexadecan-1-amine Chemical compound CCCCCCCCCCCCCCCCN(CCCCCCCCCCCCCCCC)CCCCCCCCCCCCCCCC LYYLWJOKAQADDU-UHFFFAOYSA-N 0.000 claims description 2
DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 claims description 2
DYFFAVRFJWYYQO-UHFFFAOYSA-N n-methyl-n-phenylaniline Chemical compound C=1C=CC=CC=1N(C)C1=CC=CC=C1 DYFFAVRFJWYYQO-UHFFFAOYSA-N 0.000 claims description 2
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
229920000570 polyether Polymers 0.000 claims description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 claims description 2
RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 claims description 2
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims description 2
239000008096 xylene Substances 0.000 claims description 2
150000003738 xylenes Chemical class 0.000 claims description 2
YWWDBCBWQNCYNR-UHFFFAOYSA-N trimethylphosphine Chemical compound CP(C)C YWWDBCBWQNCYNR-UHFFFAOYSA-N 0.000 claims 2
KNKRKFALVUDBJE-UHFFFAOYSA-N 1,2-dichloropropane Chemical compound CC(Cl)CCl KNKRKFALVUDBJE-UHFFFAOYSA-N 0.000 claims 1
239000000654 additive Substances 0.000 claims 1
230000000996 additive effect Effects 0.000 claims 1
MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 claims 1
RYVBINGWVJJDPU-UHFFFAOYSA-M tributyl(hexadecyl)phosphanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[P+](CCCC)(CCCC)CCCC RYVBINGWVJJDPU-UHFFFAOYSA-M 0.000 claims 1
RXJKFRMDXUJTEX-UHFFFAOYSA-N triethylphosphine Chemical compound CCP(CC)CC RXJKFRMDXUJTEX-UHFFFAOYSA-N 0.000 claims 1
ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 claims 1
KCTAHLRCZMOTKM-UHFFFAOYSA-N tripropylphosphane Chemical compound CCCP(CCC)CCC KCTAHLRCZMOTKM-UHFFFAOYSA-N 0.000 claims 1
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract 2
230000002152 alkylating effect Effects 0.000 abstract 1
229910000073 phosphorus hydride Inorganic materials 0.000 abstract 1
NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 8
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 7
239000000203 mixture Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
150000001721 carbon Chemical group 0.000 description 5
238000004817 gas chromatography Methods 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
238000004821 distillation Methods 0.000 description 3
239000012071 phase Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
150000008044 alkali metal hydroxides Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000012159 carrier gas Substances 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000001307 helium Substances 0.000 description 2
229910052734 helium Inorganic materials 0.000 description 2
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 2
230000014759 maintenance of location Effects 0.000 description 2
229940050176 methyl chloride Drugs 0.000 description 2
125000001453 quaternary ammonium group Chemical group 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
RNHKXHKUKJXLAU-UHFFFAOYSA-N 2-(4-methylphenyl)acetonitrile Chemical compound CC1=CC=C(CC#N)C=C1 RNHKXHKUKJXLAU-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
CYENPVHSVXTNPT-UHFFFAOYSA-N CC(C1=CC=CC=C1)(C)C#N.CC1=CC=C(CC#N)C=C1.C(C1=CC=CC=C1)C#N Chemical compound CC(C1=CC=CC=C1)(C)C#N.CC1=CC=C(CC#N)C=C1.C(C1=CC=CC=C1)C#N CYENPVHSVXTNPT-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
230000003266 anti-allergic effect Effects 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
NEHMKBQYUWJMIP-NJFSPNSNSA-N chloro(114C)methane Chemical compound [14CH3]Cl NEHMKBQYUWJMIP-NJFSPNSNSA-N 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
238000001514 detection method Methods 0.000 description 1
125000003963 dichloro group Chemical group Cl* 0.000 description 1
238000000605 extraction Methods 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002366 halogen compounds Chemical class 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
239000012535 impurity Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
JZMJDSHXVKJFKW-UHFFFAOYSA-N methyl sulfate Chemical compound COS(O)(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-N 0.000 description 1
230000001035 methylating effect Effects 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
150000004714 phosphonium salts Chemical class 0.000 description 1
239000001294 propane Substances 0.000 description 1
NNOBHPBYUHDMQF-UHFFFAOYSA-N propylphosphine Chemical compound CCCP NNOBHPBYUHDMQF-UHFFFAOYSA-N 0.000 description 1
238000010791 quenching Methods 0.000 description 1
230000000171 quenching effect Effects 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/60—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D211/62—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4
- C07D211/64—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals attached in position 4 having an aryl radical as the second substituent in position 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Chemical Kinetics & Catalysis (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Hydrogenated Pyridines (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

CZ19984148A 1997-12-17 1998-12-15 Způsob přípravy alkylovaných kyanoderivátů v přítomnosti trialkylaminů nebo trialkylfosfinů CZ293875B6 (cs)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE1997156091 DE19756091A1 (de)	1997-12-17	1997-12-17	Verfahren zur Alkylierung von Alkyl- oder Benzylcyanderivaten in Gegenwart von Trialkylaminen oder -phosphinen
DE1998103408 DE19803408A1 (de)	1998-01-29	1998-01-29	Verfahren zur Alkylierung von Alkyl- oder Benzylcyanderivaten in Gegenwart von Trialkylaminen oder -phosphinen

Publications (2)

Publication Number	Publication Date
CZ414898A3 CZ414898A3 (cs)	1999-07-14
CZ293875B6 true CZ293875B6 (cs)	2004-08-18

Family

ID=26042529

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CZ19984148A CZ293875B6 (cs)	1997-12-17	1998-12-15	Způsob přípravy alkylovaných kyanoderivátů v přítomnosti trialkylaminů nebo trialkylfosfinů

Country Status (22)

Country	Link
US (1)	US6143896A (da)
EP (1)	EP0924196B1 (da)
JP (2)	JP4410329B2 (da)
KR (1)	KR100589305B1 (da)
CN (1)	CN1119322C (da)
AR (1)	AR016435A1 (da)
AT (1)	ATE243191T1 (da)
AU (1)	AU740310B2 (da)
BR (1)	BR9805350B1 (da)
CA (1)	CA2256941C (da)
CZ (1)	CZ293875B6 (da)
DE (1)	DE59808753D1 (da)
DK (1)	DK0924196T3 (da)
ES (1)	ES2200260T3 (da)
HU (1)	HU221417B1 (da)
ID (1)	ID21458A (da)
NO (1)	NO317334B1 (da)
NZ (1)	NZ333375A (da)
PL (1)	PL194500B1 (da)
PT (1)	PT924196E (da)
TR (1)	TR199802607A2 (da)
UA (1)	UA64711C2 (da)

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* Cited by examiner, † Cited by third party
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KR100886002B1 (ko) *	2004-01-30	2009-03-03	유로-셀띠끄 소시에떼 아노님	4-테트라졸릴-4-페닐피페리딘 화합물의 제조방법
BRPI1006780A2 (pt)	2009-04-01	2019-03-26	Lek Pharmaceuticals D. D.	processo para preparar um composto, processo para a preparação de 3-amino-2, 2-dimetilpropanamida,processo para preparar um agente terapêutico, profilático ou de diagnóstico, processo para preparar alisquireno, processo para preparar um derivado de criptoficina,uso de um composto,uso de 3-amino-2,2-dimetilpropanamida e uso de agente terapêutico,profilático ou de diagnóstico.
CN109694334B (zh) *	2017-10-23	2022-07-22	西华大学	双取代氰基乙酸酯化合物的无溶剂制备方法
CN109694335B (zh) *	2017-10-23	2021-12-17	西华大学	双取代对硝基苯乙腈衍生物的无溶剂制备方法
CN109694333A (zh) *	2017-10-23	2019-04-30	西华大学	双取代丙二腈衍生物的无溶剂制备方法

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3668255A (en) *	1967-10-31	1972-06-06	Rhodia	Process for alkylation of aliphatic ketones and product
DE2206778A1 (de) *	1972-02-12	1973-08-16	Bayer Ag	Verfahren zur herstellung von bisalkylierten organischen verbindungen
JPS5163145A (en) *	1974-11-26	1976-06-01	Sumitomo Chemical Co	33 mechiru 22 * 44 harogenofueniru * buchironitoriruno seizoho
US4254129A (en) *	1979-04-10	1981-03-03	Richardson-Merrell Inc.	Piperidine derivatives
JPS57185252A (en) *	1981-05-07	1982-11-15	Nippon Tokushu Kagaku Kogyo Kk	Production of phenylacetonitrile derivative
US4377531A (en) *	1981-10-07	1983-03-22	American Cyanamid Company	Method for the alkylation of phenylacetonitriles
JPH06234668A (ja) *	1993-02-10	1994-08-23	Nippon Steel Corp	９，９−ジアルキルフルオレンの製造方法
DE4407495A1 (de) *	1994-03-07	1995-09-14	Basf Ag	Verfahren zur Methylierung organischer Verbindungen

1998
- 1998-12-09 PT PT98123418T patent/PT924196E/pt unknown
- 1998-12-09 DK DK98123418T patent/DK0924196T3/da active
- 1998-12-09 EP EP98123418A patent/EP0924196B1/de not_active Expired - Lifetime
- 1998-12-09 DE DE59808753T patent/DE59808753D1/de not_active Expired - Lifetime
- 1998-12-09 AT AT98123418T patent/ATE243191T1/de active
- 1998-12-09 ES ES98123418T patent/ES2200260T3/es not_active Expired - Lifetime
- 1998-12-15 NZ NZ333375A patent/NZ333375A/xx not_active IP Right Cessation
- 1998-12-15 TR TR1998/02607A patent/TR199802607A2/xx unknown
- 1998-12-15 ID IDP981630A patent/ID21458A/id unknown
- 1998-12-15 AR ARP980106374A patent/AR016435A1/es active IP Right Grant
- 1998-12-15 CZ CZ19984148A patent/CZ293875B6/cs not_active IP Right Cessation
- 1998-12-15 UA UA98126635A patent/UA64711C2/uk unknown
- 1998-12-15 HU HU9802909A patent/HU221417B1/hu unknown
- 1998-12-16 CA CA002256941A patent/CA2256941C/en not_active Expired - Lifetime
- 1998-12-16 AU AU97142/98A patent/AU740310B2/en not_active Expired
- 1998-12-16 NO NO19985895A patent/NO317334B1/no not_active IP Right Cessation
- 1998-12-16 BR BRPI9805350-7A patent/BR9805350B1/pt not_active IP Right Cessation
- 1998-12-16 US US09/212,585 patent/US6143896A/en not_active Expired - Lifetime
- 1998-12-17 JP JP35886898A patent/JP4410329B2/ja not_active Expired - Fee Related
- 1998-12-17 CN CN98125573A patent/CN1119322C/zh not_active Expired - Lifetime
- 1998-12-17 PL PL330376A patent/PL194500B1/pl unknown
- 1998-12-17 KR KR1019980055570A patent/KR100589305B1/ko not_active Expired - Lifetime
2009
- 2009-09-17 JP JP2009215412A patent/JP4976472B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DE59808753D1 (de)	2003-07-24
PL330376A1 (en)	1999-06-21
CN1222505A (zh)	1999-07-14
ID21458A (id)	1999-06-17
JPH11263766A (ja)	1999-09-28
CA2256941C (en)	2009-09-01
JP4976472B2 (ja)	2012-07-18
CA2256941A1 (en)	1999-06-17
NO317334B1 (no)	2004-10-11
ES2200260T3 (es)	2004-03-01
DK0924196T3 (da)	2003-09-29
CN1119322C (zh)	2003-08-27
AU740310B2 (en)	2001-11-01
HUP9802909A1 (hu)	1999-09-28
EP0924196A1 (de)	1999-06-23
JP4410329B2 (ja)	2010-02-03
HK1020568A1 (en)	2000-05-12
TR199802607A3 (tr)	1999-07-21
JP2010018619A (ja)	2010-01-28
TR199802607A2 (xx)	1999-07-21
NO985895D0 (no)	1998-12-16
HU9802909D0 (en)	1999-02-01
AR016435A1 (es)	2001-07-04
HUP9802909A3 (en)	2000-06-28
BR9805350A (pt)	2000-03-21
CZ414898A3 (cs)	1999-07-14
KR19990063143A (ko)	1999-07-26
ATE243191T1 (de)	2003-07-15
PT924196E (pt)	2003-11-28
UA64711C2 (uk)	2004-03-15
PL194500B1 (pl)	2007-06-29
AU9714298A (en)	1999-07-08
NO985895L (no)	1999-06-18
KR100589305B1 (ko)	2006-10-19
EP0924196B1 (de)	2003-06-18
BR9805350B1 (pt)	2009-12-01
US6143896A (en)	2000-11-07
NZ333375A (en)	2000-05-26
HU221417B1 (en)	2002-09-28

Legal Events

Date	Code	Title	Description
2000-06-30	PD00	Pending as of 2000-06-30 in czech republic
2018-12-27	MK4A	Patent expired	Effective date: 20181215

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AU2004212038B2 (en)	2010-11-25	Process for preparing pyridine-substituted amino ketal derivatives
MXPA98010704A (en)	1999-09-20	Procedure for the alquilation of alkilcian or bencilcian derivatives in the presence of trialquilamines or trialquilfosfi
JP3995116B2 (ja)	2007-10-24	Ｎ−アルケニルアゾールの製造
Binmore	1995	Free radical rearrangements of cyclohexa-2.5-diene derivatives and strained polycyclic compounds
DE19803408A1 (de)	1999-08-05	Verfahren zur Alkylierung von Alkyl- oder Benzylcyanderivaten in Gegenwart von Trialkylaminen oder -phosphinen
HK1020568B (en)	2003-12-24	Process for the alkylation of alkyl-or benzylcyanogen derivatives in the presence of trialkylamines or-phosphines
JPS62273953A (ja)	1987-11-28	４−アリルオキシ−２，２，６，６−テトラアルキルピペリジン誘導体の製法
JP2003286254A (ja)	2003-10-10	光学活性環状アルコールの製造方法